Fearlessly tackling every genre, the exceptional Bruce Willis has crafted an outstanding Hollywood resume throughout his 40-year career. After achieving widespread fame with his role in the 80s comedy-drama series Moonlighting, the seasoned performer went on to become a worldwide action hero following his role as the sarcastic John McClane in the epic 1988 flick Die Hard. He would go on to star in a slew of dynamic and critically-acclaimed pictures, showing off his natural gift for humor in popular flicks like Look Who’s Talking, Red, and Cop Out.
Updated June 3rd, 2023: If you’re a Bruce Willis fan, then you’ll be happy to know that this article was recently updated by Amanda Minchin.
Willis has undoubtedly been a jack of all trades in the entertainment business, having worked with revered directors like Wes Anderson, Robert Zemeckis, and Robert Rodriguez. He has proven time and time again that he’s far more than just a brooding leading man, demonstrating his comedic chops and undeniable star power throughout his enviable career. His sardonic delivery of lines and willingness to embrace the strange have helped make him one of the most successful box offices draws of all time.
Wills recently announced his retirement following a recent health diagnosis. The body of work he leaves behind is beyond impressive. With over one hundred TV series and films under his belt, the impact he’s had on the industry would be difficult to miss. He is truly hilarious and undeniably one of a kind. Willis’ innate ability to inject even the most serious of action movies with witty, sarcastic humor sets him apart in the comedy world (and also makes it difficult to separate his action films from his comedy films). Regardless of genre, these films show Bruce Willis at his funniest.
12 The Expendables
The Expendables is a juggernaut action-comedy franchise. Written and directed by none other than Sylvester Stallone, this team-up of (mostly) aging action heroes is a massive supernova of star power, full of punchy phrases and straight-up punches. Willis co-starred alongside the likes of Sylvester Stallone, Jason Statham, Dolph Lundgren, Jet Li, and Arnold Schwarzenegger as the enigmatic Mr. Church, who is named after his primary place of business. His role served as the catalyst for sending the mercenary group on their quest.
The role had proven difficult to cast. Schwarzenegger declined in favor of his smaller cameo, as did Kurt Russell, who was not interested in ensemble acting at the time. After several months of principal photography, Willis agreed to join the cast. While his role in the franchise is perhaps not the funniest on this list, the sheer number of quips littered throughout the film more than makeup for it. There is an uncanny sense of déjà vu from having one too many action heroes in one room that just brings a smile to one’s face. Unfortunately, Willis was sorely missed just a few years later when he did not return for the series’ third outing in 2014. Even having the illustrious Harrison Ford as his replacement was not enough to save the third film.
11 The Whole Nine Yards
Bruce Willis and Matthew Perry teamed up to star in the 2000 crime comedy The Whole Nine Yards, which tells the story of the charismatic but unhappy dentist Nicholas “Oz” Oseransky. Oz makes the startling discovery that his new next-door neighbor Jimmy is actually a notorious Chicago contract killer with a large bounty on his head. At the insistence of his money-hungry wife, Oz decides to inform the mob boss of his whereabouts in exchange for the reward.
Willis showed off his comedic chops in the entertaining picture, brilliantly portraying gangster Jimmy “the Tulip” Tudeski and showcasing an undeniable on-screen chemistry with Perry. The actor would later famously guest star on Friends after having lost a bet to Perry after The Whole Nine Yards topped the box office. The two later teamed up for the sequel, The Whole Ten Yards.
10 Pulp Fiction
Pulp Fiction is nothing short of a cult classic, not only for igniting and reinvigorating the careers of several of its stars but for its downright quirkiness to boot. Written and directed by none other than Quentin Tarantino, the movie follows four stories of violence and crime in L.A. in non-chronological order. The name of the film is a nod to the sensational crime novels and magazines of the early 20th century that were known for their graphic violence and quick-witted dialogue. Arguably, the tone of the film followed suit.
In the movie, Willis played the role of prizefighter Butch Coolidge, which was initially intended for Matt Dillon. Willis was a huge fan of Tarantino’s Reservoir Dogs at the time and was keenly interested in taking part in one of Tarantino’s next films. Though he’d initially asked about several other characters, Tarantino choose Willis as Butch because of his undeniable 50s character look. The film arguably reignited Willis’ career following a series of flops, setting him up for success in several films shortly thereafter.
As a man of few words, the character of Butch didn’t do a heck of a lot of talking throughout the course of the movie. The lines he does say, however, are full of humor and wit in even the most dire of scenarios (and boy, do they get dire). It’s hard not to feel for this character as we follow him through what is, without a doubt, the single weirdest day of his life. Pulp Fiction isn’t a straight-out comedy, so that is why it is ranked a little lower than one might expect, but there is no doubt the movie does have some incredible humorous moments in it.
9 Look Who’s Talking
Bruce Willis showed off his impressive vocal talents he hilariously portrayed the narrating baby Mikey in the 1989 romantic comedy Look Who’s Talking. As a talking baby, Willis offered amusing commentary on the state of his mother, Mollie’s love life, and her blossoming relationship with her suitor James. Co-starring John Travolta and Kirstie Alley, this rom-com was a surprise hit at the box office and went on to earn $297 million, spawning two popular sequels and the short-lived ABC sitcom Baby Talk.
8 Cop Out
Bruce Willis teamed up with the always hilarious Tracy Morgan for the 2010 buddy cop action-comedy Cop Out, in which the entertaining duo portray seasoned NYPD partners Jimmy Monroe and Paul Hodges. The pair set out to investigate the theft of Jimmy’s highly-coveted, mint-condition baseball card that was stolen by a memorabilia-connoisseur gangster.
While there was no shortage of drama during the production and aftermath of the comedy (Willis and director Kevin Smith notoriously butted heads), Cop Out still went on to become one of Smith’s most financially successful projects to date, showcasing some seriously comical on-screen chemistry between Willis and Morgan. In a reversal, Smith publicly apologized for his disparaging past comments towards Willis in the wake of the actor’s retirement from filmmaking.
7 Planet Terror
The innovative Robert Rodriguez-helmed 2007 action horror comedy Planet Terror follows a shabby group of biochemical outbreak survivors who are forced to fend off a terrifying horde of zombie-like creatures in rural Texas. Funny, right? Longtime Rodriguez friend and collaborator Quentin Tarantino helped bring the freaky film to life, with plenty of notes for the actor’s performances along the way.
Bruce Willis appeared alongside actors Rose McGowan and Josh Brolin in this horror comedy. He amusingly portrayed the deranged Lieutenant Muldoon, a man who contributed to the gruesome zombie outbreak. The filmmaker’s use of Willis was also a nod to the Grindhouse genre. Back in the day, Grindhouse makers would contract a big-name star for a day and place them prominently on the poster after to garner more revenue. Looking closely, it appears Willis was not in frame with the other actors in the film, which is in keeping with that aesthetic. Grindhouse filmmakers would often get a few frontal shots of the big man on campus on their day of hire and fill in any gaps with a body double.
6 Over the Hedge
In addition to his more action-heavy roles, Bruce Willis has also shared the animated spotlight, dabbling in his fair share of roles made strictly for kids, from Spike the Dog in Rugrats Go Wild to a stint in The Lego Movie 2: The Second Part. Over the Hedge, however, is probably one of Willis’ most well-known roles of the bunch. In the film, Willis plays RJ, a fast-talking raccoon who is way over his head as the leader of a group of animals whose land has been encroached upon by the suburbs.
While the covert ops in Willis’ films typically require less forest and more firepower, this is still one of his funniest roles. The jokes are mixed, with several that would likely go over many a young person’s head. However, the visual of Willis as an animated raccoon is simply too hilarious to pass up.
Red touted a star-studded cast of Hollywood acting elite, from Bruce Willis to Morgan Freeman and Helen Mirren. This 2010 action comedy centered around retired black-ops agent Frank Moses (Willis) as he leaves his quiet suburban life and reassembles his old team in order to defeat a high-tech assassin… all while bringing his new-found crush along for the ride. Tagged as R.E.D. (Retired, Extremely Dangerous), the squad must once again put their special skills to good use in order to break into CIA headquarters and expose an enormous conspiracy in the process.
This film’s mix of action-packed humor proved a crowd-pleaser. Loosely based on the Homage Comics series of the same name, Red went on to become a critical and commercial hit, grossing $199 million at the box office and leading to a 2013 sequel.
4 The Last Boy Scout
The 1991 buddy action comedy The Last Boy Scout features an impressive cast, including Bruce Willis, Damon Wayans, and Halle Berry. Considered one of the best films directed by Tony Scott, the movie follows private investigator Joe Hallenbeck as he warily finds himself joining forces with the boyfriend of a female witness he was hired to protect.
Despite an initially mixed reaction by critics, the flick was still a box office success and helped Willis recover his cinema star status after the failure of his other comedy project, Hudson Hawk, that same year. The film has since garnered a passionate following as a 90s cult classic. The sharp screenplay, delightful chemistry between Willis and Wayans, and the overall direction of the movie come highly praised.
3 Death Becomes Her
Death Becomes Her tells the spellbinding story of a narcissistic, fading actress who discovers a magic potion that grants them eternal youth and immortality. Robert Zemeckis directed, and Meryl Streep, Goldie Hawn, and Bruce Willis starred in this perfect horror comedy. The renowned actresses portrayed life-long frenemies vying for the affection of the same man (Willis). Both take the potion in hopes of winning him over.
This film is widely regarded as a pioneer for its impressive use of computer-generated effects (it was the first to use photo-realistic human skin software). Death Becomes Her has gone on to acquire a prominent following, especially in the LGBTQ+ community.
2 Moonrise Kingdom
Renowned filmmaker Wes Anderson directed the 2012 coming-of-age comedy-drama Moonrise Kingdom, which tells the heartwarming tale of two 12-year-olds who fall in love in 1965. Soon, they decide to run away from their coastal New England town. The island’s police captain Sharp (Bruce Willis), bans together with a group of peculiar residents to track down the love-struck kids and bring them safely home. The dramedy premiered at the Cannes Film Festival, where it garnered universal acclaim, with high marks from the BBC, among others.
Willis opened up about the Oscar-nominated picture and, working with Anderson, calling it one of the projects he’s most proud of, saying, “Moonrise Kingdom is a very novel story. There’s nothing like it, except another Wes Anderson film. And even in his library, I think he would say, too, that Moonrise Kingdom was really different than anything he has ever done,”.
1 Die Hard
Bruce Willis became a certified movie star after he memorably portrayed iconic, wise-cracking New York City police detective John McClane in the 1988 action classic Die Hard. The film follows the reluctant hero as he faces off against German terrorists who have taken a Los Angeles skyscraper hostage. Famous for his biting one-liners, including his beloved famous catchphrase, “Yippee-ki-yay, motherfu**er!” Willis provided hilarious and colorful commentary as he begrudgingly fights to take down villain Hans Gruber.
The result is brilliantly entertaining every step of the way. Willis’ performance in this 80s staple also helped redefine the face of the action genre. The actor’s portrayal of McClane inspired a new wave of everyday heroes, average characters who manage to save the day with physique and sardonic humor to boot… all while personifying a one-man army in the process.